Record Information
Version1.0
Creation date2010-04-08 22:15:24 UTC
Update date2019-11-26 03:19:45 UTC
Primary IDFDB021009
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1,2,2'-Trisinapoylgentiobioside
Description1,2,2'-Trisinapoylgentiobioside belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives. 1,2,2'-Trisinapoylgentiobioside is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,2,2'-Trisinapoylgentiobioside is found, on average, in the highest concentration within broccoli. 1,2,2'-Trisinapoylgentiobioside has also been detected, but not quantified in, brassicas. This could make 1,2,2'-trisinapoylgentiobioside a potential biomarker for the consumption of these foods.
CAS Number155380-01-1
Structure
Thumb
Synonyms
SynonymSource
2-{[3,4-dihydroxy-5,6-bis({[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy})oxan-2-yl]methoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acidGenerator
1,2,2'-Trisinapoylgentiobiosidedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.058 g/LALOGPS
logP2.84ALOGPS
logP2.54ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)8.81ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area323.81 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity231.76 m³·mol⁻¹ChemAxon
Polarizability96.49 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC45H52O23
IUPAC name6-{[(4,5-dihydroxy-3-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)oxan-2-yl)oxy]methyl}-4,5-dihydroxy-3-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}oxan-2-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
InChI IdentifierInChI=1S/C45H52O23/c1-57-24-13-21(14-25(58-2)35(24)50)7-10-32(47)66-42-40(55)38(53)30(19-46)64-44(42)63-20-31-39(54)41(56)43(67-33(48)11-8-22-15-26(59-3)36(51)27(16-22)60-4)45(65-31)68-34(49)12-9-23-17-28(61-5)37(52)29(18-23)62-6/h7-18,30-31,38-46,50-56H,19-20H2,1-6H3/b10-7+,11-8+,12-9+
InChI KeyHVHNDGOZMSAQDC-SRDSWEMOSA-N
Isomeric SMILESCOC1=CC(\C=C\C(=O)OC2OC(COC3OC(CO)C(O)C(O)C3OC(=O)\C=C\C3=CC(OC)=C(O)C(OC)=C3)C(O)C(O)C2OC(=O)\C=C\C2=CC(OC)=C(O)C(OC)=C2)=CC(OC)=C1O
Average Molecular Weight960.8806
Monoisotopic Molecular Weight960.28993797
Classification
Description Belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acid glycosides
Alternative Parents
Substituents
  • Hydroxycinnamic acid glycoside
  • O-cinnamoyl glycoside
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • Tricarboxylic acid or derivatives
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Styrene
  • Alkyl aryl ether
  • Fatty acid ester
  • Phenol
  • Oxane
  • Benzenoid
  • Monocyclic benzene moiety
  • Fatty acyl
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Acetal
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Ether
  • Primary alcohol
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 56.25%; H 5.45%; O 38.30%DFC
Melting PointMp 155-158°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0abi-0092011704-b6efc5f7262894214506Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-0292040602-6f70e08ae89e7bb4a36cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0290000000-046277b57e1c16840dc4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052u-0041030905-488156d433b4c849caa1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7u-0196070604-5b0c09ccc992abdbb164Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05s1-0154070922-964dc29ea9eee5d858d6Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID512
DrugBank IDNot Available
HMDB IDHMDB41127
CRC / DFC (Dictionary of Food Compounds) IDCPD88-P:NJK55-N
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.